Literature DB >> 27431372

FeCl3 -Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.

Lina Ma1, Wenjuan Li1, Hui Xi1, Xiaohui Bai1, Enlu Ma1, Xiaoyu Yan1, Zhiping Li2.   

Abstract

Exploiting catalytic carbonyl-olefin metathesis is an ongoing challenge in organic synthesis. Reported herein is an FeCl3 -catalyzed ring-closing carbonyl-olefin metathesis. The protocol allows access to a range of carbo-/heterocyclic alkenes with good efficiency and excellent trans diastereoselectivity. The methodology presents one of the rare examples of catalytic ring-closing carbonyl-olefin metathesis. This process is proposed to take place by FeCl3 -catalyzed oxetane formation followed by retro-ring-opening to deliver metathesis products.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; carbocycles; heterocycles; iron; metathesis

Year:  2016        PMID: 27431372     DOI: 10.1002/anie.201604349

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  21 in total

1.  Synthesis of 2H-Chromenes via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.

Authors:  Yunfei Zhang; Janis Jermaks; Samantha N MacMillan; Tristan H Lambert
Journal:  ACS Catal       Date:  2019-09-10       Impact factor: 13.084

2.  Recent advances in the application of ring-closing metathesis for the synthesis of unsaturated nitrogen heterocycles.

Authors:  Emilia J Groso; Corinna S Schindler
Journal:  Synthesis (Stuttg)       Date:  2019-02-08       Impact factor: 3.157

3.  Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis.

Authors:  Yunfei Zhang; Jae Hun Sim; Samantha N MacMillan; Tristan H Lambert
Journal:  Org Lett       Date:  2020-07-15       Impact factor: 6.005

4.  Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction.

Authors:  Jacob R Ludwig; Susan Phan; Christopher C McAtee; Paul M Zimmerman; James J Devery; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-07-28       Impact factor: 15.419

5.  Lewis Acid Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Jacob R Ludwig; Corinna S Schindler
Journal:  Synlett       Date:  2017       Impact factor: 2.454

6.  Catalyst Behavior in Metal-Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Carly S Hanson; Mary C Psaltakis; Janiel J Cortes; James J Devery
Journal:  J Am Chem Soc       Date:  2019-07-22       Impact factor: 15.419

7.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

Authors:  Emilia J Groso; Alexander N Golonka; Ryan A Harding; Brandon W Alexander; Taylor M Sodano; Corinna S Schindler
Journal:  ACS Catal       Date:  2018-01-18       Impact factor: 13.084

8.  Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy.

Authors:  Carly S Hanson; James J Devery
Journal:  J Vis Exp       Date:  2020-02-20       Impact factor: 1.355

9.  Investigation of Lewis Acid-Carbonyl Solution Interactions via Infrared-Monitored Titration.

Authors:  Carly S Hanson; Mary C Psaltakis; Janiel J Cortes; Sameera S Siddiqi; James J Devery
Journal:  J Org Chem       Date:  2019-12-27       Impact factor: 4.354

10.  Lewis acid-catalyzed carbonyl-olefin metathesis.

Authors:  Paul S Riehl; Corinna S Schindler
Journal:  Trends Chem       Date:  2019-03-15
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